


Handcuffs and Strip Searches

by Saiyurimai



Category: Undertale (Video Game)
Genre: Alternate Universe, Alternate Universe - Gangsters, Alternate Universe - Police, Angst, Based on a dream I had, Corruption, F/M, Innocent Grillby coming to the dark side, M/M, Multi, Polyamorous Character, Polyamory, Public Sex, Sai is a sneaky little shit, Sai's Friends, Seduction to the Dark Side, Smut, shennanigans, threeway
Language: English
Status: In-Progress
Published: 2019-02-16
Updated: 2019-02-16
Packaged: 2019-10-29 21:14:09
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 1
Words: 3,475
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17815634
Author URL: https://archiveofourown.org/users/Saiyurimai/pseuds/Saiyurimai
Summary: Officer Grillby was the top of his class at the academy. Now, he's one of the most crime infested districts where everything is run by a powerful and elusive monster and his charming right hand girl, Sai. Can he avoid being swayed to the deep underground criminal empire? Or is the seductive pull of Sai and her mate too hard to ignore?





	Handcuffs and Strip Searches

“-we’ve got a possible domestic disturbance on Sixth and Ninth…” The radio droned on, the flame elemental returning to the squad car with his partner.

 

 

“Alright! Nice. Thanks for the coffee man. Still can’t believe we got stuck pulling double duty tonight.” The flame elemental shrugged, he was used to it. Being a rookie got him all the crap hours but at least his partner was nice enough. He’d been showing Grillby the ropes the last few months. “Hey Grillby, we got a go on patrol now. Come on.” The human officer nodded, getting back into the driver’s seat of the patrol car while Grillby got into the passenger side, coffee in hand.

 

 

“So where’re we patrolling now?” Grillby asked as they pulled away from the coffee shop, watching and memorizing the streets as they passed them. He’d been out on patrol only a couple times, still new to the routes but he was a quick learner. Top of his class at the academy and now he was placed in one of the most crime ridden areas of the city.  

 

 

“We get the south sector, apparently there’ve been some reports of gang activity, the biggest one round here is run by a guy named Gaster.” His partner drover through the streets, the police radio chattering in the background, their eyes never stopping their scans of the streets. Grillby had heard rumors about the crime boss, had seen some reports and even a photo of the guy during his time on desk duty. “We haven’t been able to pin anything solid on the guy yet but we know he’s got his paws in just about everything that goes on in this city.” Grillby nodded, taking all the information in, it was something he knew he’d have to keep in mind since this was going to be his beat for a while.

 

 

They rounded a corner street, keeping their eyes peeled for anything suspicious. “Anything I should know when I’m out here? Like any accomplices to look out for?” He asked and when they pulled up to a stop light his partner typed in a few numbers on their computer, pulling up a screen with the face of a woman with distinctive purple and red hair. “Who’s she?”

 

 

His partner scoffed and started to drive again while Grillby looked through her rap sheet. “That’s Sai. She’s Gaster’s number one. She has the inside track on Gaster, but we haven’t been able to get close to her. The guy normally has her surrounded by body guards if she goes out, or he’s right there with her. That’s his girl, if anybody knows all his dirty little secrets, she’s the one. We get her we can bring the whole operation down for sure.” Grillby looked at her relatively tame rap sheet.

 

 

She didn’t look like the type to be associated with a crime boss. She actually looked kind of sweet with that smile of hers. She had been arrested for loitering, some shop lifting, mostly misdemeanors. Never got any jail time. But he imagined it was possible that if Gaster was as big and bad as he sounded it was possible he could get a real good lawyer for her if he needed.

 

 

“Don’t let her looks fool ya man. She’s hot but pretty sure she’s fucking crazy. She’s gotta be hangin around a guy like Gaster. Ya know one of the other guys on the force was working a homicide a few weeks ago, said the victim just looked at Sai and next day he was hanging by his toes in front of his house according to a witness.” Grillby looked at Sai’s picture and blinked in surprise. Sure she was attractive but did she really warrant outright murder for looking at her?

 

 

“Must be some girl I guess.” He mused aloud before looking up to the streets again. It was relatively quiet it seemed. The time passed slowly as they roamed the streets looking for trouble. They were just starting to near the end of their shift when they came to the front of a club, his partner slowing down and scanning the crowd leaving for the night for anyone who might be of interest to them.

 

 

“Holy shit…Grillby my man this might be our lucky fuckin night.” His partner slapped him in the chest and pointed to a small group of people, a couple of women and several tough looking men all surrounding a familiar purple and red haired woman who was in the middle of smoking a cigarette and laughing at something someone said.

 

 

“This is unit 217 requesting backup, we’ve got eyes on known suspect Sai Yurimai and several of her known body guards on Main Street just outside of The Lunar Lounge. Requesting at least three or more patrol cars to help in arrests. Over.” Grillby’s partner called it in, staying out of sight of Sai and her group of cohorts until backup arrived.

 

 

“Copy that 217, units inbound. Be there in 5. Over.” Someone on the radio called in as Grillby’s partner grabbed his bullet proof vest and slipped it on, motioning for him to do the same. 

 

 

“This is it. We bring her in and we are made. We gotta do this right rookie and we can retire heroes.” Grillby snapped his vest on, glancing up to see Sai taking a drag on her cigarette, cocking her hips in her skin tight dress with boots that covered sculpted legs that went on for days. Looking at her he never would have thought she was the girl of the biggest crime boss in the city, she was young, pretty, and there was a confidence about her. But she was a criminal, the linchpin on bringing down Gaster and his criminal empire.

 

 

He watched her move about, staying carefully within the circle of guards and scanning the area. She kept her back to the wall, making sure no one snuck up behind her, her body language putting off an easiness to the untrained eye but the more he looked, the more he realized it was all an act. She was ready to bolt if need be, or put up a fight, that much he could tell. “They’re here man. You ready?” Grillby was pulled out of his thoughts by his partner nodding to the unsuspecting group.

 

 

Grillby was one of the first few to approach, his holster ready and unhooked in case things got messy. Sai motioned towards one of her body guards who nodded and all of them seemed to close ranks, not looking aggressive, not running but very obviously upset with the end of their night. He watched her type something out quickly on her phone and put out her cigarette, before coming to approach the group of officers.

 

 

The group of women she was with dispersed quickly and hurried into cars that were already waiting for them. “Morning officers. To what do we owe this honor on this fine morning.” Her voice was sultry and smooth, totally unfazed by the number of police officers surrounding her and the bodyguards.

 

 

“You know why we’re here, now are we doing this the hard or the easy way?” One of the other officers stepped forward, his fingers poised to pull out his gun if he needed to. Grillby didn’t think she looked dangerous but sometimes the most innocent looking could be the most dangerous. “Your buddies here got a few warrants out for them and you, well, we’ve got a nice room just for you.” Sai bat her lashes and tossed her hair over her shoulder flirtatiously.

 

 

“Aw! Just for me? You shouldn’t have! But I’m afraid you don’t have any reason to bring me in. So no I won’t be going in tonight. It’s been a long day and I would really rather just head home.” It was like a game to her, Grillby wondered just how many times they’ve done this. How many times they’d gone around like this.

 

 

She adjusted her dress slightly, her gaze scanning the group of officers before finally settling on Grillby, her golden hazel eyes locking onto him like a predator hunting its prey. “Although I could make a pit stop for a handsome guy like you. What’s your name sweetheart…” She practically purred.

 

 

“Miss Sai, we really should be getting you back…” One of her body guards grumbled, looking around a little nervously, but not at the cops at something unseen in the darkened alleys. Sai waved him off with a flick of her wrist, a silver bracelet catching the light.

 

 

“Oh don’t you worry big guy. We’ve got to be good boys and girls for these lovely folks in blue. Especially this one. Isn’t that right officer…Grillby is it?” She stepped closer, she was shorter than him even with the heels by at least a foot. “Now I know you’ve got to take a couple of my guys in, that’s not a problem. They’ll go with you, right boys?” She didn’t even bother looking back at her body guards who hung their heads as a couple came forward, ready to be handcuffed and put into the patrol cars.

 

 

“Good. Now, the rest of these guys don’t have any reason to be taken in. They’re all clean I promise so no reason to bother them right?” She was talking right to Grillby, stepping as close as she could get without touching, very careful of how close she stood to him.

 

 

Grillby narrowed his gaze at her from behind his glasses, she was testing him. He knew that. A few others started to arrest Sai’s guards that had stepped forward willingly, none of them putting up a fight. This was going way too easy. She had to have something up her sleeve.

 

 

He didn’t graduate top of his class for nothing. “And what about you? Are you coming in willingly to answer some questions or are we just going to have to book you?” He asked as she smiled up at him, her hands on her hips as she shrugged nonchalantly.

 

 

“Only if you cuff me. I promise to be a good girl.” She winked and bit her hip teasingly. Something wasn’t right there but she appeared to be going in willingly. Grillby looked towards his partner who shrugged and motioned for him to continue. “Let’s go big guy. I don’t have all night.” She nodded towards his patrol car with a soft giggle.

 

 

“Go on, take her back to the station, I gotta help the others with these guys.” His partner handed him the keys to the cruiser, Sai fiddling with her phone before putting it in her dress, Grillby making sure to avert his gaze as she put the phone right at her breast and making a show of it.

 

 

“Go ahead, I’ll check in with you when you get to the station.” Grillby nodded and led Sai towards the cruiser, doing his best not to stare. She really was a beautiful woman but it was very clear that she was still dangerous. Her eyes betraying whatever feigned innocence she tried to portray.

 

 

Once they got to the patrol car he opened the backseat. “Watch your head.” She snorted and turned back to look at him.

 

 

“Thanks but it isn’t my first time being in the backseat of a cop car. But you know you should probably frisk me, put me in a pair of cuffs. You know, follow protocol.” She quirked a brow at him. She was right. He’d been so distracted he’d almost forgotten about all of that. “There we go. I knew you were a bright one. Don’t worry, I won’t tell anyone. Happens more times than you think.” She held her arms out, assuming the position for him to frisk her, make sure she didn’t have anything on her. Which, she didn’t, aside from her phone.

 

 

“No purse or anything?” He asked, most women carried one but all she had was her phone and her ID. There wasn’t even any cash. She shook her head with a grin.

 

 

“Nope. Don’t need one. Just gets in the way.” He supposed it was possible that she didn’t need it, if Gaster was her guy then she probably was known enough through whatever businesses he was in charge of to get everything she could ever want for free out of fear of retaliation. She turned around and put her palms behind her back so he could put the cuffs on her.

 

 

“Careful of the bracelet. It was a gift.” She tossed over her shoulder. It was nice, expensive looking, set with a purple stone and a pair of diamonds. Simple but pretty nonetheless. He helped her into the back of the car, Sai giving a flirtatious wink as she leaned forward enough to give him a view of her cleavage which gave a blue tinge to his flames but he cleared his throat, closing the door behind him and getting into the driver’s seat, starting the patrol car and pulling away from the scene, radioing in that he was bringing her in.

 

 

Sai sat in the backseat, watching him from the mirror with a smug grin. “You know, I’m not actually a bad person.” She stated simply as they drove. Grillby scoffed and rolled his eyes as he glanced at her from the mirror for a second

 

 

“And good folks don’t normally need to clarify that point. Although it isn’t my place to judge. I’m just a cop. You’ve got to convince a jury on that front.” He drove through the streets seeing her sit back and glance out the window with a faraway gaze. She was so calm about the whole ordeal, it set him on edge. He couldn’t figure her out, what were her motives? Why’d she come in voluntarily, and let some of her guys get arrested? Why didn’t they put up a fight? 

 

 

“Hmmm…Yeah well judge and jury can be bought. Nothing like a jury of your peers to screw you over.” She mused more like she was talking to herself. He didn’t bother responding, just glancing at her from the rear view mirror and seeing her watching the streets go by as they neared the station. She wasn’t wrong, he’d heard of corruption, and she would probably know that all too well being in her profession. “So technically I’m not under arrest correct? You just want to bring me in for questioning?” She asked, adjusting her seat to get more comfortable in the backseat. 

 

 

“Yes. Technically you’re just being brought in to answer some questions but we can detain you for about 12 hours before we have to let you go. So if you cooperate then we’ll let you go. Easy as that.” She hummed in thought and smiled, a look in her eyes that made him immediately suspicious of her questions.

 

 

She nodded and fidgeted again just as they were getting close to the station. There was a soft pop of magic and Grillby nearly swerved off the road at the appearance of a tall skeleton monster dressed sharply in a perfectly tailored suit and tie. “Ah, so this is where you’d gotten off to my pet. I thought I told you that you had to stay with the group and come right back home?” The smooth tone of the monster made Grillby hit the brakes. This was…he knew who this was. This was the W. D Gaster, biggest crime boss in town. Maybe even the state. And he was here in the backseat of his patrol car. But how? There should be no way…

 

 

“Sorry boss. This one was just so charming and sweet thought you might want to see the newbie on the force. Just look at that chiseled jaw and those broad shoulders.” Sai hummed and licked her lips with a wink to Grillby in the front seat. What the hell was he supposed to do?! He had them both in the backseat of his patrol car but he was in no way in control of the situation. Gaster chuckled and leaned in, capturing her lips in a kiss that made his cheeks blue.

 

 

“You always did have a soft spot for shoulders. But, it’s late and you need to go to bed. If you want to talk to her you can contact her lawyer. Otherwise, I’ll be taking my property back thank you very much. It was a pleasure meeting you Officer Grillby. I’m sure it won’t be the last time.” Gaster winked and a business card landed on his dash with the name of one of the best lawyers in town printed on it.

 

 

“I hope you don’t mind but I’m going to be borrowing your handcuffs, I’m afraid they look far too good on my girl here to take them off. Plus it saves me a bit of extra time. And I am nothing if not efficient.” Sai gasped and giggled, the sound turning to a moan that went straight to Grillby’s loin despite his best effort as Gaster pulled Sai under him, mouth nipping at her throat in one second, the two gone with a pop of magic in the next.

 

 

Leaving a flabbergasted and flustered Grillby sitting open mouthed looking at his now empty backseat. “What the actual fuck just happened?!” He blinked, driving into the station and getting out of the car, grabbing the business card off the dash and slamming the door. Now he was going to have to explain what happened to his higher ups and that was not going to go over well…not in the least.

 

 

“So, how’d it go?” Came a drawling familiar tone from the front of his car. That was Stretch, he’d been in the same class as him at the academy but he’d been in this district for a little while longer than him. He was currently rolling a honey flavored lollipop between his teeth, seeing as how he wasn’t allowed to smoke on the grounds. Not that it would matter much since he was a skeleton and cigarettes wouldn’t actually hurt his nonexistent lungs. But there were humans that worked here too.  

 

 

Grillby grumbled and sighed, rubbing his face. “I had her in the back, and then Gaster showed up and poof they were both gone! He gave me his lawyer’s card and that was it! I am so screwed…” Stretch popped the lollipop out of his mouth and grabbed the business card from him, looking it over.

 

 

“Hm. How far did you get her to the station before he came to pick her up?” He asked, not seeming at all perturbed that they’d just lost two of their biggest catches. In fact he seemed completely at ease, popping the candy back in his mouth.

 

 

“Less than a block away. I could see the gate. I was this close! How’d he even manage it? I searched her. She didn’t have anything on her and her phone was off.” Stretch eyed him with a look of slight surprise. “What? Why aren’t you more upset about this?”

 

 

Stretch shook his head with a chuckle. “I’ve been here long enough to know that they’ve been trying for months to try and get Sai anywhere near the police station but every single time her handler always comes to fetch her. We can’t pin anything on her. Because she hasn’t done anything wrong. We can’t prove that she knows what he’s doing or all his dealings and that he’s just his shiny plaything. The closest they’ve managed to get her was about six blocks away. They have a pool going in the office on who can get her to the actual station.” Stretch handed him back the business card and jerked his thumb towards the main bullpen.

 

 

“She must’ve really liked you to let you take her as far as you did. Pretty sure you won this week’s pool.” Grillby was confused. Sure Sai seemed charming but so charming that the force seemed to be so lackadaisical about her disappearing into thin air? That was a new one for him. That’s for sure. He followed Stretch into the bull pen and gave his report to the chief who only laughed and handed over the couple hundred bucks from the pool. He wasn’t in trouble. Apparently this was a regular enough occurrence that they’d made it a game.

 

 

By the end of his shift he made his way to his crappy apartment above a bar, fresh with some cash from the pool, after adding some back for the next week’s pool. He had to wonder. Just what was it about that one woman that had so many of them eating out of the palms of her hand? And why couldn’t he get the sound of her moan out of his dreams…


End file.
